1-碘-2-(辛氧甲基)苯 | 1160063-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-碘-2-(辛氧甲基)苯
• 英文名称: 1-iodo-2-(octyloxymethyl)benzene
• 英文别名: 2-iodo-1-(octyloxymethyl)benzene；1-iodo-2-octyloxymethylbenzene；2-iodobenzyl heptyl ether；1-Iodo-2-(octoxymethyl)benzene
• CAS: 1160063-30-8
• 化学式: C₁₅H₂₃IO
• 分子量: 346.252
• InChiKey: YYJIVBWLPXXORM-UHFFFAOYSA-N

物化性质

• 沸点：
  356.3±17.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-碘-2-(辛氧甲基)苯 在 (1,3-dimethylimidazol-2-ylidene)borane 、 di-tert-butoxydiazene 、 苯硫酚 作用下， 以 苯 为溶剂， 反应 3.0h， 以86%的产率得到(辛基氧基)甲基苯
  参考文献：
  名称：

  N-杂环卡宾硼烷自由基还原卤化物的极性反转催化

  摘要：

  否则，N-杂环卡宾硼烷（NHC-硼烷）对烷基和芳基卤化物的缓慢或完全无效的自由基还原由硫醇催化。使用容易获得的 1,3-二甲基咪唑-2-亚基硼烷和水溶性三唑相关物的还原和还原环化反应由苯硫酚和叔十二烷硫醇催化 [C(9)H(19)C(CH(3))(2 )SH]。苯硫基 (PhS•) 自由基与两个 NHC 硼烷反应的速率常数已通过激光闪光光解实验测量为 ~10(8) M(-1) s(-1)。对现有证据的分析表明极性反转催化的作用。

  DOI：

  10.1021/ja300416f
• 作为产物：
  描述：

  1-碘辛烷 、 2-碘苄醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以71%的产率得到1-碘-2-(辛氧甲基)苯
  参考文献：
  名称：

  Platinum and Ruthenium Chloride-Catalyzed Cycloisomerization of 1-Alkyl-2-ethynylbenzenes: Interception of π-Activated Alkynes with a Benzylic C−H Bond

  摘要：

  Air-stable and commercially available alkynophilic metal salts, such as PtCl2, PtCl4, and [RuCl2(CO)(3)](2), catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce Substituted indenes even at all ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-H bonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.

  DOI：

  10.1021/jo901045g

文献信息

• Boryltrihydroborate: Synthesis, Structure, and Reactivity as a Reductant in Ionic, Organometallic, and Radical Reactions
  作者：Kyoko Nozaki、Yoshitaka Aramaki、Makoto Yamashita、Shau-Hua Ueng、Max Malacria、Emmanuel Lacôte、Dennis P. Curran

  DOI：10.1021/ja105277u

  日期：2010.8.25

  dimer lacks the bridging B-H bonds seen in neutral boranes and is instead held together by ionic Li---HB interactions. A preliminary scan of reactions with several iodides shows that the compound participates in an ionic reduction (with a primary-alkyl iodide), an organometallic reduction (Pd-catalyzed with an aryl iodide), and a radical reduction (AIBN-initiated with a sugar-derived iodide). Accordingly

  锂 1,3-双(2,6-二异丙基苯基)-2,3-二氢-1H-1,3,2-二氮杂硼醇-2-ide 与硼烷反应。THF 提供了第一个硼基取代的硼氢化物：锂 [1 ,3-双(2,6-二异丙基苯基)-2,3-二氢-1H-1,3,2-二氮杂硼醇-2-基]三氢硼酸盐。该化合物通过 (11)B、(1)H 和 (7)Li NMR 光谱和其他方法进行了充分表征，并将这些数据与中性和阴离子基准化合物进行了比较。该化合物结晶为与四个 THF 分子复合的二聚体。二聚体缺乏在中性硼烷中看到的桥接 BH 键，而是通过离子 Li---HB 相互作用结合在一起。对几种碘化物反应的初步扫描表明，该化合物参与了离子还原（用伯烷基碘）、有机金属还原（用芳基碘催化的钯）、和自由基还原（AIBN 由糖衍生的碘化物引发）。因此，新的硼基硼氢化物类可能具有传统硼氢化物和等电子 N-杂环卡宾硼烷的特性。
• Ionic and Organometallic Reductions with N-Heterocyclic Carbene Boranes
  作者：Qianli Chu、Malika Makhlouf Brahmi、Andrey Solovyev、Shau-Hua Ueng、Dennis P. Curran、Max Malacria、Louis Fensterbank、Emmanuel Lacôte

  DOI：10.1002/chem.200902450

  日期：2009.12.7

  Surgical reduction: N‐Heterocyclic carbene–borane complexes such as depicted are neutral, organic soluble analogues of borohydride anions with a weak hydridic character, compatible with organometallic catalysis. They are applicable for surgical reductions in complex, multifunctional molecules.

  外科手术还原：如图所示，N-杂环卡宾-硼烷络合物是硼氢化物阴离子的中性有机可溶类似物，具有较弱的氢化特性，可与有机金属催化相容。它们适用于通过手术减少复杂的多功能分子。
• Suzuki−Miyaura Coupling of NHC−Boranes: A New Addition to the C−C Coupling Toolbox
  作者：Julien Monot、Malika Makhlouf Brahmi、Shau-Hua Ueng、Carine Robert、Marine Desage-El Murr、Dennis P. Curran、Max Malacria、Louis Fensterbank、Emmanuel Lacôte

  DOI：10.1021/ol902012c

  日期：2009.11.5

  Complexes of triaryl- and trialkylboranes with N-heterocyclic carbenes (NHCs) participate in Suzuki-Miyaura cross-coupling reactions and provide coupled products in good yields under base-free conditions. The reaction can be applied to CSp(2)-CSp(2) and Csp(2)-Csp(2) carbon-carbon bond formation with triflates, iodides, bromides, and chlorides. These results enrich the utility of NHC-borane complexes, which can be added to the toolkit of Suzuki-Miyaura cross-couplings, along with boronic acids and organotrifluoroborates.
• Disulfides and Boryl Sulfides Serve as both Initiators and Precatalysts in Radical Reductions of Halides by an N‐Heterocyclic Carbene⋅Borane
  作者：Xiangcheng Pan、Jacques Lalevée、Emmanuel Lacôte、Dennis P. Curran

  DOI：10.1002/adsc.201300752

  日期：2013.12.16

  AbstractDiphenyl disulfide (PhSSPh), a typical boryl monosulfide (diiPr‐Imd‐BH2SPh) and a typical boryl bis‐sulfide [diMe‐Imd‐BH(SPh)2] all serve as both initiators and precatalysts in the reduction of alkyl and aryl halides by readily available 1,3‐dimethylimidazol‐2‐ylidene⋅borane (diMe‐Imd‐BH3). The reactions are suggested to occur by a polarity reverse catalysis mechanism where in situ generated thiophenol is the active catalyst.magnified image